US2328455A - N-alkali metal-n, n-dihalogen acylsulphanilamides - Google Patents

Description

against certain .types of. bacteria.

, halogen;

Patented Aug. 31, 1943 N -ALKALI METAL-NhNt-DIHALOGEN ACYLSULPHANILAMIDES Martin Everett Hultquist,--Plainfield, and- Moses L. Crossley,'Bound Brook, N. .J.,';assignors to American Cyanamid Company. New York, N. Y.. a corporation of Maine NoDrawing. Application July 2, 1942,

' Serial No. 449,476

9 Claims.

This .inventionrelates to a new type of sulphanilamide derivative containing active. halogen.

The activity of sulphanilamide against many bacteria has rendered it desirable to utilize it as an antiseptic. However,,the action of sulphanilamide is selective and it is eifective only Derivatives have been sought which would have more general antiseptic or germicidal action. It is;to this type of derivative that the present invention relates.

According to the present invention -N -acylsulphanilamides are produced containing active These compounds have germicidal action which is not sharply'selective as in the case of sulphanilamide. The compounds of the present invention may be considered as N -alkali metal N ,N -dihalogen N -acylsulphanilamides of p the following formula:

Hal

Hal Me in which R isra hydrocarbon radical, Hal is an active halogen such as chlorine or bromine, and Me is an alkali metal. The compounds are quite soluble which is another important characteristic of practical germicides. For the sake of cheapness, the chlorine and sodium compounds are preferred, although the bromine compounds are equally effective and, of course, the other alkali metal compounds such as the potassium compounds are of substantially the same solubility and effectiveness. R may be a hydrocarbon radical of the aliphatic or aryl series, but for best results it should be an aliphatic radical having a moderate number of carbon atoms, the compounds where R is C3H1 being preferred. The product claims are not intended to be limited to any particular method of preparation, but in a more specific aspect a preferred process consists of treating N -acylsulphanilamide with an alkali metal hydrochloride.

The invention will be described in greater detail in conjunction with the following specific examples in which the parts are by weight.

EXAMPLE 1 N -sodium-N fl -dichloro-N -butanoylsulphanilamide c1 omornomooN-Osom I 01 Na 36 parts of N -butanoyl sulphanilamide are added to 300 parts of sodium hypochlorite solution containing 12% of active chlorine. A clear solution results and oncooling to 10 C. crystals separate out and are filtered off. The solid is then dissolved in about 500 parts of Water at C., the solution filtered and 150 parts of saturated salt solution added. On cooling to 10 C. filtering and washing with cold saturated sodium chloride solution, a crystalline .product is obtained in the form of light tan needles. The product does not have any sharp melting point as it decomposes on melting at about -150 C. Titration for active chlorine with sodium thiosulphate after adding potassium iodide and acetic, acid shows about-98% purity. The product is contaminated with a small amount of sodium chloride.

EXAMPLE 2 N -sodium-N ,N -dichloro-N -acetylsulphanilamide Cl Na 107 parts N -acetylsulphanilamide are slurried in 250 parts of water, and to this is added a 350 part portion of sodium hypochlorite solution containing 12% active chlorine, maintaining the temperature at 20-25 with cooling in a water bath. A light brown solution results, and on standing, leaf-like crystals separate and are filtered oil.

The solid is dissolved in 300 parts of water at 60, the solution is filtered and cooled to 10, and the crystals are filtered and Washed with a little ice-cold water. The almost colorless crystals are dried in a vacuum dessicator.

Titration of a sample for active chlorine with sodium thiosulphate after dissolving in water and treating with potassium iodide and acetic acid shows 99.5% purity. The product does not have any sharp melting point, but decomposes vigorously at 200-210 C.

EXAMPLE 3 N -sod ium-N ,N -dichZoro-N -benzoylsulphanilamide 84 parts of N -benzoylsulphanilamide are slurried in 200 parts water, and to this is added a 300 part portion of sodium hypochlorite solu- The solid is dissolved in 500 parts of The wet f Titration, 10

in which R is a hydrocarbon radical and Me is an alkali metal.

4. N -alkali metal N ,N dichloro N acylsulphanilamide having the following probable formula:

Rr-G o NOS OQN/ in-which: R1 is an alkyl radical, and Me is an alkali metal.

and acetic acid shows 99.4% purity. The product. does not, show any sharp melting point, I but.

darkens gradually at ISO-160 and decomposes Weclaim:

1. N -alkali metal-N ,N sulphanilamide having the following probable formula:

Hal

7 Hal Me in which R is a hydrocarbon radical, Hal is a member of the group consisting of chlorine and bromine, and Me is an alkali metal.

2. N -a1kali metal N ,N dihalogen-N -acylsulphanilamide having the following probable formula: r

'/Hal RFCQIFOSO N Hal 7 Me in which R1 is an alkyl radical, Hal is a member of the group consisting of chlorine or bromine, and Me is an alkali metal. a

3, N -alkali metal N ,N dichloro N acylsulphanilamide having the following probable formula:

RG ONOS o N dihalogen-N -acy I v N5. :N sodium N N dichloro N butanoylsulphanilamide having the following probable formula:

omon on oonOso r 6. N -sodium N ,N -dich1oro N -acetylsulp anilamide having. the following probable formula: V 1 l CHaC ON SO N l Na ' -'l. N1 -s0dium-N ,N -dichloro-N -benzoylsulphanilamide formula:

' o1 Na having the following probable SpA method of preparing N -alka1i metal- N ,N -diha1ogen-N -acylsulphanilamide which comprises reacting the corresponding N -acylsulphanilamide with an alkali metal hypohalite.

9. A method of preparing -N -alkali metal- N ,N dichloro N acylsulphanilamide' which comprises reacting the corresponding N -acylsulphanilamide with an alkali metal hypoohlorite.

MARTIN EVERETT HUL'IQUIST.

- osEsnoRossLEY.